U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O5
Molecular Weight 360.4448
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CORTISONE

SMILES

C[C@@]12CCC(=O)C=C2CC[C@@]3([H])[C@]4([H])CC[C@](C(=O)CO)([C@@]4(C)CC(=O)[C@@]31[H])O

InChI

InChIKey=MFYSYFVPBJMHGN-ZPOLXVRWSA-N
InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H28O5
Molecular Weight 360.4448
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: http://www.wikidoc.org/index.php/Cortisone | https://www.drugs.com/pro/cortisone-acetate.html | https://www.ncbi.nlm.nih.gov/pubmed/2811372 | https://www.ncbi.nlm.nih.gov/pubmed/7358829 | https://books.google.com/books?id=Q1voCAAAQBAJ&pg=PA113&lpg=PA113&dq=CORTISONE+SULFATE&source=bl&ots=-bwZTb4Fzh&sig=4gjBk9MhoF8OrL-7I5c06Fr32A8&hl=en&sa=X&ved=0ahUKEwiblMuT9pfVAhXK4SYKHXKKB6wQ6AEITTAG#v=onepage&q=CORTISONE%20SULFATE&f=false | http://www.google.com.pg/patents/US20120135924 | http://www.google.com.pg/patents/US20120128785 | https://www.google.com/patents/US4450151

Cortisone is a hormone that is FDA approved for the treatment of primary and secondary adrenocortical deficiency, rheumatic disorders, psoriasis, exfoliative dermatitis, bronchial asthma, allergic conjunctivitis, hemolytic anemia, enteritis, tuberculosis, trichnosis. Cortisone acetate binds to the cytosolic glucocorticoid receptor. After binding the receptor, the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. Common adverse reactions include convulsions, increased intracranial pressure with papilledema, vertigo, headache, psychic disturbances, hirsuitism, glaucoma, exophthalmos. Aminoglutethimide may lead to a loss of corticosteroid-induced adrenal suppression. Co-administration of corticosteroids and warfarin usually results in inhibition of response to warfarin, although there have been some conflicting reports. Cortisone is a natural steroid hormone. Its sulfate analog has been detected in in umbilical vein blood fetus plasma between 19 and 32 weeks of gestation with a significant increase at 29-30 weeks and in amniotic fluid. Base on the experiments with rats it was suggested that cortisone sulfate in mammals could be hydrolyzed enzymatically liberating sulfate ions from cortisone. Cortisone sulfate has been proposed for use as one of the glycosaminoglycan compound materials in a cartilage prosthesis and biological nasal bridge implant manufacture as well as auxiliary agent in powder aerosol composition for use in baby powder, dry shampoo, water-eczema remedy and antiperspirant.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SOLU-CORTEF

Approved Use

Treatment of the Allergic states, Dermatologic diseases, Endocrine disorders, Gastrointestinal diseases, Hematologic disorders, Neoplastic diseases, Rheumatic disorders, Respiratory diseases, Renal diseases, Ophthalmic diseases, Nervous System

Launch Date

-463363200000
Primary
SOLU-CORTEF

Approved Use

Treatment of the Allergic states, Dermatologic diseases, Endocrine disorders, Gastrointestinal diseases, Hematologic disorders, Neoplastic diseases, Rheumatic disorders, Respiratory diseases, Renal diseases, Ophthalmic diseases, Nervous System.

Launch Date

-463363200000
Primary
SOLU-CORTEF

Approved Use

When oral therapy is not feasible, and the strength, dosage form, and route of administration of the drug reasonably lend the preparation to the treatment of the condition, the intravenous or intramusculat use of SOLU-CORTEF Sterile Powder is indicated as follows: Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the drug of choice).

Launch Date

-463363200000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
477 nM
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CORTISONE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1211 nM × h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CORTISONE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4109 nM × h
44.8 mg 1 times / day steady-state, oral
dose: 44.8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CORTISONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
23 min
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CORTISONE plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
16.2%
CORTISONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: MALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Corticosteroid sulfates in fetus plasma.
1989 Oct
Chemotherapy-related hemolytic-uremic syndrome following treatment of a carcinoma of the nasopharynx.
2001
15-ketodihydro-PGF2 alpha, progesterone and cortisol profiles in heifers after induction of parturition by injection of dexamethasone.
2001
Fetal endocrine signals and preterm labor.
2001
Male-female differences in rat hypothalamic-pituitary-adrenal axis responses to nicotine stimulation.
2001 Apr
20beta-Hydroxysteroid dehydrogenase of the Japanese eel ovary: its cellular localization and changes in the enzymatic activity during sexual maturation.
2001 Apr
Expression of 11 beta-hydroxysteroid dehydrogenase isozymes and corticosteroid hormone receptors in primary cultures of human trophoblast and placental bed biopsies.
2001 Apr
The adrenal and the metabolic syndrome.
2001 Apr
[Transitory neonatal diabetes].
2001 Apr
Light and electron microscopy localization of the 11beta-hydroxysteroid dehydrogenase type I enzyme in the rat.
2001 Apr
[A woman with Addison's disease and a bump on the neck].
2001 Apr 20
Regression of neovascular iris vessels by intravitreal injection of crystalline cortisone.
2001 Aug
Guidance by ultrasound of intra-articular injections in the knee and hip joints.
2001 Aug
Efficacy of nonoperative treatment for lateral epicondylitis.
2001 Aug
[Idiopathic thrombocytopenia during pregnancy. The risk in connection with umbilical blood sampling is probably greater than the benefit].
2001 Aug 8
Increased ACTH levels do not alter renal 11beta-hydroxysteroid dehydrogenase type 2 gene expression in the sheep.
2001 Feb
Smooth muscle tumor developing in an immunocompromised child after therapy for leukemia.
2001 Feb
Steroids differentially inhibit the nicotinic acetylcholine receptor.
2001 Feb 12
[Serious life events and congenital malformations. A national study with a complete follow-up].
2001 Feb 19
Lack of mutations of type 1 11beta-hydroxysteroid dehydrogenase gene in patients with abdominal obesity.
2001 Feb-May
Direct effect of thyroxine on pig sphincter of Oddi contractility.
2001 Jan
Neuroendocrine consequences of very early weaning in swine.
2001 Jan
Antiviral drugs in chronic hepatitis B: review and meta-analysis.
2001 Jan
Human cervical tissue metabolizes the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, via alpha-hydroxylation and carbonyl reduction pathways.
2001 Jan
Induction of p53 expression in skin by radiotherapy and UV radiation: a randomized study.
2001 Jan 17
Phenotypic analysis of mice bearing targeted deletions of 11beta-hydroxysteroid dehydrogenases 1 and 2 genes.
2001 Jan 22
Serum cortisol/cortisone ratio after Synacthen stimulation.
2001 Jul
Effects of growth hormone replacement on cortisol metabolism in hypopituitary patients treated with cortisone acetate.
2001 Jul
The intracellular localization of the mineralocorticoid receptor is regulated by 11beta-hydroxysteroid dehydrogenase type 2.
2001 Jul 27
Activation of the hypothalamic-pituitary-adrenal axis in obesity: cause or consequence?
2001 Jun
New ideas for medical treatment of congenital adrenal hyperplasia.
2001 Mar
Defective cortisone 11-oxoreductase activity?
2001 Mar
Heterogeneity within medullary-type TCRalphabeta(+)CD3(+)CD4(-)CD8(+) thymocytes in normal mouse thymus.
2001 Mar
Induction of 11beta-hydroxysteroid dehydrogenase type 1 but not -2 in human aortic smooth muscle cells by inflammatory stimuli.
2001 May
Witness to a miracle: the initial cortisone trial: an interview with Richard Freyberg, MD. Interview by Mary Ellen Warner.
2001 May
Sarcoidosis: old and new treatments.
2001 May
Aqueous chromatography utilizing pH-/temperature-responsive polymer stationary phases to separate ionic bioactive compounds.
2001 May 1
Oxidized glucocorticoids counteract glucocorticoid-induced apoptosis in murine thymocytes in vitro.
2001 May 18
Calcium inhibits human placental 11beta-hydroxysteroid dehydrogenase type 2 activity.
2001 May 18
The immune haemolytic anaemias: a century of exciting progress in understanding.
2001 Sep
Glucocorticoid metabolism and adrenocortical reactivity to ACTH in myotonic dystrophy.
2001 Sep
Intraocular injection of crystalline cortisone as adjunctive treatment of diabetic macular edema.
2001 Sep
Patents

Sample Use Guides

Therapy is initiated by administering hydrocortisone sterile powder intravenously over a period of 30 seconds (e.g., 100 mg) to 10 minutes (e.g., 500 mg or more). In general, high dose corticosteroid therapy should be continued only until the patient’s condition has stabilized, usually not beyond 48 to 72 hours.
Route of Administration: Other
With the highest concentration of cortisone that can be used under these conditions (owing to the limitation of solubility), namely 10 ug/ml., it is only possible to kill about 50 % of the lymphocytes in 46 hr; and, by extrapolation of the curve, that a concentration of about 10 mg/ml. would be required to kill 99 % of them.
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:16:52 UTC 2021
Edited
by admin
on Sat Jun 26 08:16:52 UTC 2021
Record UNII
V27W9254FZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CORTISONE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CORTISONE [USP-RS]
Common Name English
PREDNISONE IMPURITY A [EP]
Common Name English
17,21-DIHYDROXYPREGN-4-ENE-3,11,20-TRIONE
Systematic Name English
PREGN-4-ENE-3,11,20-TRIONE, 17,21-DIHYDROXY-
Systematic Name English
CORTISONE [WHO-DD]
Common Name English
CORTISONE [INN]
Common Name English
HYDROCORTISONE IMPURITY B [EP]
Common Name English
NSC-9703
Code English
CORTISONE [MI]
Common Name English
CORTISONE [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175576
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
LOINC 14159-8
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
WHO-VATC QS01BA03
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
WHO-ATC H02AB10
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
WHO-ATC S01BA03
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
NCI_THESAURUS C2323
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
LIVERTOX 239
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
LOINC 14044-2
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
WHO-VATC QH02AB10
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
LOINC 30511-0
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
LOINC 74360-9
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
LOINC 30072-3
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
LOINC 25382-3
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
NDF-RT N0000175450
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
Code System Code Type Description
EPA CompTox
53-06-5
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL1650
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
PUBCHEM
222786
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
INN
1368
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
DRUG BANK
DB14681
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
EVMPD
SUB06807MIG
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
MERCK INDEX
M3795
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY Merck Index
RXCUI
2878
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
CORTISONE
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
CAS
53-06-5
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
NCI_THESAURUS
C395
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
FDA UNII
V27W9254FZ
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
LACTMED
Cortisone
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
MESH
D003348
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-162-4
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY
USP_CATALOG
1149999
Created by admin on Sat Jun 26 08:16:53 UTC 2021 , Edited by admin on Sat Jun 26 08:16:53 UTC 2021
PRIMARY USP-RS
Related Record Type Details
PARENT -> METABOLITE
MINOR
URINE
METABOLITE ACTIVE -> PARENT
Metabolite to parent drug ratio in non-uraemic human plasma.
METABOLITE TO PARENT DRUG RATIO
PLASMA
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY